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Academy Advisor, Steppingstone Scholars Program

Position Overview
The Academy Advisor for the Steppingstone Scholars Program will work collaboratively on a small team to support the successful execution of this program. This multifaceted role blends supporting the academic and social-emotional needs of middle school students with program design and implementation. The Advisor will develop deep knowledge of the Boston educational landscape as well as the resources available to assist students and families in navigating their journey to college. In collaboration with the team, the Advisor will support the delivery of the after-school, Saturday, and summer sessions. As a result, some Saturday and evening work is required.

The Advisor will work a Tuesday-Saturday schedule during the school year and a Monday-Friday schedule during the summer months. Wednesday afternoons during the school year end around 7:00 p.m., and occasional additional evening work is mandatory. 

This summer, Steppingstone will host a 5-week in-person program for Scholars, which will be held at Milton Academy. The Advisor must be able to work in person at Milton Academy. Following the summer session, the Advisor will work from home for most of the week, with some (yet to be determined) time in the office. The format of Steppingstone’s academic year programming with Scholars is still to be determined. 

Responsibilities:

Advising
  • Advise a cohort of 25-30 fifth and/or sixth grade Scholars and their families 
  • Collaborate with teachers and program staff to develop strategies to support students’ academic and social growth using a restorative approach
  • Offer families resources to support student development
  • Teach social emotional classes in the summer and at Saturday sessions

School Placement 
  • Support students through a right fit school selection process for 6th or 7th grade including, but not limited to, the independent and/or exam school application process
  • Guide families to make informed decisions about educational choices 
  • Serve as a liaison to independent schools and facilitate relationship-building between school admission offices and Steppingstone 

Program Implementation
  • Work with team to ensure safe and efficient operation of after-school, Saturday, and summer sessions 
  • Support the development and execution of program climate/culture, reflected in preventative structures and socio-emotional curriculum, community and family events, and behavior management systems
  • Plan and implement family meetings and other large events to disseminate information to and build community among families 

Other projects
  • With the assistance of program leadership, use effective systems to track and analyze student progress and program results, including a database and data-tracking tools
  • Contribute to other cross-team office-wide efforts such as curriculum development, the admission process, and internal task forces and committees

Required Knowledge and Skills:
  • Demonstrated commitment to educational and racial equity in college access and success
  • Experience working with upper elementary or middle school students, incorporating cross-cultural competency to support and challenge them appropriately
  • Teaching experience in a classroom or out-of-school time setting
  • Experience as an effective team member in a collegial environment
  • Strong relationship-building and group facilitation skills across differing stakeholders
  • Effective project management skills with demonstrated initiative, flexibility, and problem-solving capabilities
  • Strong attention to detail and process management
  • Bachelor’s degree
  • Preference given to candidates who are bilingual in Spanish, Vietnamese, Arabic, or Chinese (Mandarin or Cantonese) 
  • Knowledge of independent schools and/or Boston Public Schools is a plus 

Starting Salary: $40,500

To Apply: 
Please input your resume and a thoughtful cover letter outlining how your skills and experience meet the qualifications of the position, and how you learned about this position, by following this link and selecting “Academy Advisor, Steppingstone Scholars Program.” Applications will be reviewed on a rolling basis. 


Steppingstone Core Values

Power of One
  • We honor every voice and believe we are strongest when we work together.
  • We recognize, respect, and nurture the fullness and complexity of each member of our community.
  • We believe in the power of belonging and seek to create a welcoming and inclusive culture.

Walk the Walk
  • We partner with every Scholar and family, supporting them holistically throughout their own educational journey.
  • We work with clear and measurable purpose, using data to drive collective decision-making and challenge assumptions.
  • We create spaces for difficult conversations to transform our thinking and move us forward.

Embrace Growth
  • We strive to operate as an anti-racist organization and commit to continuous learning and action in the service of this goal.
  • We provide opportunities for everyone in our community to flourish and reach their full potential.
  • We make time for reflection, learn from past experiences, and take initiative in response to changing needs and new ideas.

The Steppingstone Foundation is an equal opportunity employer and will not discriminate 
against any individual, employee, or application for employment on the basis of race, color, 
marital status, religion, age, sex, sexual orientation, national origin, or handicap, as defined by law.